Cu-Catalyzed Reaction of Trifluoromethylated β-Keto Diazos and Nitriles Proceeding via H2O Addition to Nitrile Ylides

Mei, Haibo and Du, Youlong and Wang, Qian and Escorihuela, Jorge and Kiss, Loránd and Soloshonok, Vadim A. and Han, Jianlin (2024) Cu-Catalyzed Reaction of Trifluoromethylated β-Keto Diazos and Nitriles Proceeding via H2O Addition to Nitrile Ylides. Advanced Synthesis and Catalysis. ISSN 1615-4150

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Abstract

A Cu-catalyzed multi-component reaction of trifluoromethylated β-amino ketones and nitriles using tert-butyl nitrite as a diazotization reagent has been developed. Under the optimized conditions, N-trifluoroalkyl amides were obtained with yields up to 87%. Control experiments and computational studies reveal that the reaction proceeds through the generation of diazo, in situ formation of nitrile ylide, water addition and final enol tautomerism. This approach features mild reaction conditions, wide substrate tolerance, and scale-up applicability, which provides an efficient and practical strategy for amide synthesis.

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